- 1,6-Diaminoperylene bisimide with a highly twisted perylene core
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1,6-Diaminoperylene bisimide (1) was synthesized and characterized by single-crystal X-ray diffraction. To the best of our knowledge, this is the first time that the structure of 1,6-disubstituted perylene bisimide has been reported. The crystal belongs to triclinic, space group P-1, with a = 10.3966(10), b = 15.3398(16), c = 16.8495(17) ?, α = 79.490(4)°, β = 87.055(3)°, γ = 79.423(3)°, and Z = 2. Compound 1 possesses two intramolecular C–H ?N hydrogen bonds, which generate two S(6) ring motifs. The central perylene core of 1 is twisted with dihedral angles of 19.48(2) ° and 19.50(2) °; this twist configuration induces the axial chirality in this family of perylene bisimide chromophores. Density functional theory (DFT) calculations also show that the core twist angles of 1,6-diaminoperylene bisimide are larger than those of 1,7-diaminoperylene bisimide, which may account for the fact that the 1,7-regioisomer has a more extended effective conjugation length than the 1,6-regioisomer. [Figure not available: see fulltext.]
- Chang, Che-Wei,Chien, Fang-Yun,Hu, Jiun-Wei,Tsai, Hsing-Yang,Chen, Kew-Yu
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- 1,6- and 1,7-regioisomers of dinitro- and diamino-substituted perylene bisimides: Synthesis, photophysical and electrochemical properties
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1,6- and 1,7-regioisomers of dinitro- (1,6-3 and 1,7-3) and diamino-substituted perylene bisimides (1,6-1 and 1,7-1) were synthesized. The regioisomers 1,6-3 and 1,7-3 were successfully separated by high performance liquid chromatography and characterized
- Tsai, Hsing-Yang,Chang, Che-Wei,Chen, Kew-Yu
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p. 884 - 888
(2014/02/14)
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- 1,6- and 1,7-regioisomers of dinitro- and diamino-substituted perylene bisimides: Synthesis, photophysical and electrochemical properties
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1,6- and 1,7-regioisomers of dinitro- (1,6-3 and 1,7-3) and diamino-substituted perylene bisimides (1,6-1 and 1,7-1) were synthesized. The regioisomers 1,6-3 and 1,7-3 were successfully separated by high performance liquid chromatography and characterized
- Tsai, Hsing-Yang,Chang, Che-Wei,Chen, Kew-Yu
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p. 884 - 888
(2015/02/19)
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- 1,6- and 1,7-Regioisomers of asymmetric and symmetric Perylene Bisimides: Synthesis, characterization and optical properties
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The 1,6- and 1,7-regioisomers of dinitro- (1,6-A and 1,7-A) and diamino-substituted perylene bisimides (1,6-B and 1,7-B), and 1-Amino-6-nitro- and 1-Amino-7-nitroperylene bisimides (1,6-C and 1,7-C) were synthesized. The 1,6-A and 1,7-A regioisomers were
- Tsai, Hsing-Yang,Chang, Che-Wei,Chen, Kew-Yu
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p. 327 - 341
(2014/02/14)
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- 1,7-Diaminoperylene bisimides: Synthesis, optical and electrochemical properties
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A series of blue dyes, 1,7-diaminoperylene bisimides (2a-2c), was synthesized under mild condition in high yields, and was characterized by 1H NMR, UV-Vis, HRMS spectra, cyclic voltammetry, differential scanning calorimetry, and thermogravimetr
- Tsai, Hsing-Yang,Chen, Kew-Yu
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p. 319 - 327
(2013/02/22)
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